Granisetron

Base Information

• Chemical Name: Granisetron
• CAS No.: 124998-65-8
• Deprecated CAS: 121061-98-1
• Molecular Formula: C₁₈H₂₄N₄O
• Molecular Weight: 312.415
• European Community (EC) Number: 686-533-5
• UNII: WZG3J2MCOL
• DSSTox Substance ID: DTXSID0023111
• Nikkaji Number: J258.427A
• Wikipedia: Granisetron
• Wikidata: Q596708,Q76295197
• NCI Thesaurus Code: C62031
• RXCUI: 26237
• Pharos Ligand ID: JN6YSV9J359Y
• ChEMBL ID: CHEMBL399538,CHEMBL1290003
• Mol file: 124998-65-8.mol

Synonyms:1-Methyl-N-(endo-9-Methyl-9-Azabicyclo(3.3.1)non-3-yl)-1H-Indazole-3-Carboxamide;1H-Indazole-3-carboxamide, 1-methyl-N-(9-methyl-9-azabicyclo(3.3.1)non-3-yl;1H-Indazole-3-carboxamide, 1-methyl-N-(9-methyl-9-azabicyclo(3.3.1)non-3-yl)-, endo-;BRL 43694;BRL 43694A;BRL-43694;BRL-43694A;BRL43694;BRL43694A;Granisetron;Granisetron Hydrochloride;Granisetron Monohydrochloride;Hydrochloride, Granisetron;Kytril;Monohydrochloride, Granisetron

Chemical Property of Granisetron

Chemical Property:

• PSA: 50.16000
• LogP: 2.64720
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 312.19501140
• Heavy Atom Count: 23
• Complexity: 442

Purity/Quality:

1-Methyl-n-(9-methyl-9-azabicyclo[3.3.1]non-3-yl)-indazole-3-carboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CCCC1CC(C2)NC(=O)C3=NN(C4=CC=CC=C43)C
• Isomeric SMILES: CN1[C@@H]2CCC[C@H]1CC(C2)NC(=O)C3=NN(C4=CC=CC=C43)C
• Recent ClinicalTrials: Safety Study of Repeat Doses of SUSTOL in Adults
• Recent EU Clinical Trials: GRANISETRON TRANSDERMAL SYSTEM (GTDS) IN PREVENTING NAUSEA AND VOMITING INDUCED BY CISPLATIN-BASED CHEMOTHERAPY AND CONCURRENT RADIOTHERAPY FOR HEAD AND NECK CANCER
• Recent NIPH Clinical Trials: Prospective Study Evaluating Efficacy and Safety of Olanzapine and Aprepitant for Cisplatin-induced Nausea and Vomiting in Hepatic Arterial Infusion Chemotherapy for Hepatocellular Carcinoma

Technology Process of Granisetron

There total 14 articles about Granisetron which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

endo-N-(9-methyl-9-azabicyclo<3.3.1>nonan-3-yl)-1H-indazole-3-carboxamide (107007-95-4) + methyl iodide (74-88-4) → granisetron (109889-09-0,124998-65-8,121061-98-1,1364914-39-5)

Guidance literature:

With sodium hydroxide; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

Reference yield: 89.0%

endo-N-(9-methyl-9-azabicyclo<3.3.1>nonan-3-yl)-1H-indazole-3-carboxamide (107007-95-4) + carbonic acid dimethyl ester (616-38-6) → granisetron (109889-09-0,124998-65-8,121061-98-1,1364914-39-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; Reflux;

DOI:10.1021/acschemneuro.6b00192

Reference yield: 81.0%

1-methyl-1H-indazole-3-carboxylic acid (50890-83-0) + endo-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine (76272-41-8,141650-55-7,76272-56-5) → granisetron (109889-09-0,124998-65-8,121061-98-1,1364914-39-5)

Guidance literature:

With 4-(2-(1,3-dioxa-3a1,8,10-triaza-2,3a,14b-triboradibenzo[fg,op]tetracen-2-yl)phenyl)benzo[c]pyrimido[4,5-e][1,2]azaborinin-6(5H)-ol; In toluene; at 85 ℃; for 16h; Molecular sieve;

DOI:10.1002/chem.201900715

upstream raw materials:

endo-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine

1-methylindazole-3-carboxylic acid chloride

1-methyl-1H-indazole-3-carboxylic acid

granisetron hydrochloride

Downstream raw materials:

endo-N-(9-azabicyclo[3.3.1]non-3-yl)-1-methyl-1H-indazole-3-carboxamide hydrochloride

granisetron hydrochloride

Refernces

• 1、 Opie, Christopher R.,Noda, Hidetoshi,Shibasaki, Masakatsu,Kumagai, Naoya. "All Non-Carbon B3NO2 Exotic Heterocycles: Synthesis, Dynamics, and Catalysis". supporting information. p. 4648 - 4653. Retrieved 2019/03/17.
• 2、 Mu, Linjing,Müller Herde, Adrienne,Rüefli, Pascal M.,Sladojevich, Filippo,Milicevic Sephton, Selena,Kr?mer, Stefanie D.,Thompson, Andrew J.,Schibli, Roger,Ametamey, Simon M.,Lochner, Martin. "Synthesis and Pharmacological Evaluation of [11C]Granisetron and [18F]Fluoropalonosetron as PET Probes for 5-HT3 Receptor Imaging". . p. 1552 - 1564. Retrieved 2016/11/29.